Xjegjt a altwegq and paul pivot



Patented May 6, 1924.

IBM

- JEAN ..LTWEGG AND PAUL PIVOT, OF LYON, FRANCE, ASSIGNORS T CHIMIQ'UE 19m USINES: DU RHONE, OF ?ARIS, FRANCE.

a cartels,-

scorers PROCESS FOR THE PRODUCTION O13 DIETHYLCHLORACETAMIDE.

l lo Brewing.

To all whom it may concern: Be it known that we, JEAN Amwneo, residing al: Lyon, Rhone, France, a citizen of the Republic of Switzerland, and PAUL 5 Pryor, residing at Lyon, Rhone, France, a

citizen of the Republic of France, have-invented certain nea and useful Improvements in Processes for the Production of Diethylchloracetamide, of which the follow- 10 ing is a specification. Among the derivatives of urea and the amides of brominated fatt acids, there is a series of compounds Whlch are valuable on account of their hypnotic pro 'erties (as, .for example, adalin, bromura neuronal.and so on). l In these compounds when the bromine is replaced by chlorine, substances are obtained the narcotic efiect ofwhich is reduced.

and in consequence they have not been used in therapeutics (see Fraenkel Die Arzneimitelsynthese, 4th edn.', bottom of page 471 The surprisin fact has now bGBD'dlSCOV': ered that diethy lehloracetami'de is considerably moreeifectiye than the corresponding bromine derivative and in addition has the valuable property of producing very rapidly a deep sleep followed by a tranquil awakening.

These properties, which could not haye been foreseen,'have probably their source in the relatively easy solubility of these compounds in water. Whereas 1 litre of water dissolves 8.7 gr. of the corresponding bromi- Application tiled Hatch 8,- 1923. serial No; 623,280.

nated acid-amide, the new chlorine compound is soluble to the extent of 14-.2 gr.

The amide, which has not been previously described, can be producedfor example by treating the diethylacetylchloride with chlorine. In so doing monochlonacid chloride is obtained which is converted in a known manner into acid-amide as for example by treatment with. aqueous ammonia or a substance iving ofl ammonia, for instance, by ad ing, ammonium carbonate and warming until ammonia is liberated.

Example.

1 Mo]. diethylacetylchloride is warmed to 0., 2 atoms of chlorine are then introduced, maintaining a temperature up to about C. By distilling under a partial vacuum, the e-chlordiethylacetylchloride is obtained,in an almost theoretic yield, in the form of a li uid which passes over under a pressure of 0 m/mat 93 C.

Y By shaking this chloride with an excess of concentrated aqueous ammonia, diethyi chloracetamide is obtained quantitatively in the form of White scales, which when recrystallized melt at 58 C.

What we claim and desire to secure by Letters Patent is i As a new product, diethylchloracetamide.

vIn testimony whereof we have signed our names to this specification. 1

JEIXN PAUL PIVOT. 

